Oleoyl glycine (BioDeep_00000027053)

 

Secondary id: BioDeep_00000601968, BioDeep_00001871922

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


2-[(9Z)-octadec-9-enamido]acetic acid

化学式: C20H37NO3 (339.27732920000005)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(feces) 0.1%

分子结构信息

SMILES: CCCCCCCCC=CCCCCCCCC(=O)NCC(=O)O
InChI: InChI=1S/C20H37NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-19(22)21-18-20(23)24/h9-10H,2-8,11-18H2,1H3,(H,21,22)(H,23,24)/b10-9-

描述信息

N-oleoyl glycine is an acylglycine with oleoic acid (C18:1(9Z))moiety attached to glycine molecule. It is reported to be preferentially produced by human glycine N-acyltransferase-like 2 (hGLYATL2), a member of a gene family of 4 putative glycine conjugating enzymes, synthesizes various N-acyl glycines. Recombinantly expressed hGLYATL2 efficiently conjugated oleoyl-CoA, arachidonoyl-CoA, and other medium- and long-chain acyl-CoAs to glycine. The enzyme was specific for glycine as an acceptor molecule.
N-oleoyl glycine is an acylglycine with oleoic acid (C18:1(9Z))moiety attached to glycine molecule
N-Oleoyl glycine is a lipoamino acid, which stimulates adipogenesis associated with activation of CB1 receptor and Akt signaling pathway in 3T3-L1 adipocyte.
N-Oleoyl glycine is a lipoamino acid, which stimulates adipogenesis associated with activation of CB1 receptor and Akt signaling pathway in 3T3-L1 adipocyte.

同义名列表

12 个代谢物同义名

2-[(9Z)-octadec-9-enamido]acetic acid; N-(1-Oxo-9-octadecenyl)-(Z)-glycine; (Z)-N-(1-oxo-9-Octadecenyl)glycine; N-(9Z-octadecenoyl)-glycine; Acylglycine 18:1(9Z); N-oleoyl glycine; N-Oleoylglycine; Oleoyl glycine; Elmiric acid; Elmirate; NO-Gly; EMA-1



数据库引用编号

10 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Julia T Tanzo, Veronica L Li, Amanda L Wiggenhorn, Maria Dolores Moya-Garzon, Wei Wei, Xuchao Lyu, Wentao Dong, Usman A Tahir, Zsu-Zsu Chen, Daniel E Cruz, Shuliang Deng, Xu Shi, Shuning Zheng, Yan Guo, Mario Sims, Monther Abu-Remaileh, James G Wilson, Robert E Gerszten, Jonathan Z Long, Mark D Benson. CYP4F2 is a human-specific determinant of circulating N-acyl amino acid levels. The Journal of biological chemistry. 2023 Apr; ?(?):104764. doi: 10.1016/j.jbc.2023.104764. [PMID: 37121548]
  • Casey I Gallagher, Diba Sheipouri, Susan Shimmon, Tristan Rawling, Robert J Vandenberg. Identification of N-acyl amino acids that are positive allosteric modulators of glycine receptors. Biochemical pharmacology. 2020 10; 180(?):114117. doi: 10.1016/j.bcp.2020.114117. [PMID: 32579961]
  • Giulia Donvito, Fabiana Piscitelli, Pretal Muldoon, Asti Jackson, Rosa Maria Vitale, Enrico D'Aniello, Catia Giordano, Bogna M Ignatowska-Jankowska, Mohammed A Mustafa, Francesca Guida, Gavin N Petrie, Linda Parker, Reem Smoum, Laura Sim-Selley, Sabatino Maione, Aron H Lichtman, M Imad Damaj, Vincenzo Di Marzo, Raphael Mechoulam. N-Oleoyl-glycine reduces nicotine reward and withdrawal in mice. Neuropharmacology. 2019 04; 148(?):320-331. doi: 10.1016/j.neuropharm.2018.03.020. [PMID: 29567093]
  • Shannon N Mostyn, Tristan Rawling, Sarasa Mohammadi, Susan Shimmon, Zachary J Frangos, Subhodeep Sarker, Arsalan Yousuf, Irina Vetter, Renae M Ryan, Macdonald J Christie, Robert J Vandenberg. Development of an N-Acyl Amino Acid That Selectively Inhibits the Glycine Transporter 2 To Produce Analgesia in a Rat Model of Chronic Pain. Journal of medicinal chemistry. 2019 03; 62(5):2466-2484. doi: 10.1021/acs.jmedchem.8b01775. [PMID: 30714733]
  • Songbo Wang, Qi Xu, Gang Shu, Lina Wang, Ping Gao, Qianyun Xi, Yongliang Zhang, Qingyan Jiang, Xiaotong Zhu. N-Oleoyl glycine, a lipoamino acid, stimulates adipogenesis associated with activation of CB1 receptor and Akt signaling pathway in 3T3-L1 adipocyte. Biochemical and biophysical research communications. 2015 Oct; 466(3):438-43. doi: 10.1016/j.bbrc.2015.09.046. [PMID: 26365347]
  • Nikolaos Psychogios, David D Hau, Jun Peng, An Chi Guo, Rupasri Mandal, Souhaila Bouatra, Igor Sinelnikov, Ramanarayan Krishnamurthy, Roman Eisner, Bijaya Gautam, Nelson Young, Jianguo Xia, Craig Knox, Edison Dong, Paul Huang, Zsuzsanna Hollander, Theresa L Pedersen, Steven R Smith, Fiona Bamforth, Russ Greiner, Bruce McManus, John W Newman, Theodore Goodfriend, David S Wishart. The human serum metabolome. PloS one. 2011 Feb; 6(2):e16957. doi: 10.1371/journal.pone.0016957. [PMID: 21359215]
  • Cristiane Divan Baldani, Eduardo Hilario, Andréa Cristina Higa Nakaghi, Maria Célia Bertolini, Rosangela Zacarias Machado. Production of recombinant EMA-1 protein and its application for the diagnosis of Theileria equi using an enzyme immunoassay in horses from São Paulo State, Brazil. Revista brasileira de parasitologia veterinaria = Brazilian journal of veterinary parasitology : Orgao Oficial do Colegio Brasileiro de Parasitologia Veterinaria. 2011 Jan; 20(1):54-60. doi: 10.1590/s1984-29612011000100011. [PMID: 21439233]
  • Dominik P Waluk, Niklas Schultz, Mary C Hunt. Identification of glycine N-acyltransferase-like 2 (GLYATL2) as a transferase that produces N-acyl glycines in humans. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2010 Aug; 24(8):2795-803. doi: 10.1096/fj.09-148551. [PMID: 20305126]
  • Gregory P Mueller, William J Driscoll. Biosynthesis of oleamide. Vitamins and hormones. 2009; 81(?):55-78. doi: 10.1016/s0083-6729(09)81003-0. [PMID: 19647108]
  • Heather B Bradshaw, Neta Rimmerman, Sherry S-J Hu, Sumner Burstein, J Michael Walker. Novel endogenous N-acyl glycines identification and characterization. Vitamins and hormones. 2009; 81(?):191-205. doi: 10.1016/s0083-6729(09)81008-x. [PMID: 19647113]
  • Gregory P Mueller, William J Driscoll. In vitro synthesis of oleoylglycine by cytochrome c points to a novel pathway for the production of lipid signaling molecules. The Journal of biological chemistry. 2007 Aug; 282(31):22364-9. doi: 10.1074/jbc.m701801200. [PMID: 17537719]
  • Shalini Chaturvedi, William J Driscoll, Brenda M Elliot, Martha M Faraday, Neil E Grunberg, Gregory P Mueller. In vivo evidence that N-oleoylglycine acts independently of its conversion to oleamide. Prostaglandins & other lipid mediators. 2006 Dec; 81(3-4):136-49. doi: 10.1016/j.prostaglandins.2006.09.001. [PMID: 17085322]
  • Su Duy Nguyen, Dai-Eun Sok. Preferential inhibition of paraoxonase activity of human paraoxonase 1 by negatively charged lipids. Journal of lipid research. 2004 Dec; 45(12):2211-20. doi: 10.1194/jlr.m400144-jlr200. [PMID: 15375178]
  • David J Merkler, Geoffrey H Chew, Andrew J Gee, Kathleen A Merkler, Jean-Paul O Sorondo, Mitchell E Johnson. Oleic acid derived metabolites in mouse neuroblastoma N18TG2 cells. Biochemistry. 2004 Oct; 43(39):12667-74. doi: 10.1021/bi049529p. [PMID: 15449956]
  • Sanjay Kumar, Naoaki Yokoyama, Jung-Yeon Kim, Xiaohong Huang, Noboru Inoue, Xuenan Xuan, Ikuo Igarashi, Chihiro Sugimoto. Expression of Babesia equi EMA-1 and EMA-2 during merozoite developmental stages in erythrocyte and their interaction with erythrocytic membrane skeleton. Molecular and biochemical parasitology. 2004 Feb; 133(2):221-7. doi: 10.1016/j.molbiopara.2003.10.010. [PMID: 14698434]
  • Amani W Farah, N A M Hegazy, M M Romany, Y A Soliman, A M Daoud. Molecular detection of Babesia equi in infected and carrier horses by polymerase chain reaction. The Egyptian journal of immunology. 2003; 10(2):73-9. doi: NULL. [PMID: 15719614]
  • Xuenan Xuan, Bayin Chahan, Xiaohong Huang, Naoaki Yokoyama, Levi Hakwale Makala, Ikuo Igarashi, Kozo Fujisaki, Soich Maruyama, Takeo Sakai, Takeshi Mikami. Diagnosis of equine piroplasmosis in Xinjiang province of China by the enzyme-linked immunosorbent assays using recombinant antigens. Veterinary parasitology. 2002 Sep; 108(2):179-82. doi: 10.1016/s0304-4017(02)00193-0. [PMID: 12208045]